WO2014141620A1 - Solution électrolytique destinée à être utilisée dans un condensateur électrolytique aluminium et condensateur électrolytique aluminium qui utilise cette dernière - Google Patents

Solution électrolytique destinée à être utilisée dans un condensateur électrolytique aluminium et condensateur électrolytique aluminium qui utilise cette dernière Download PDF

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Publication number
WO2014141620A1
WO2014141620A1 PCT/JP2014/001141 JP2014001141W WO2014141620A1 WO 2014141620 A1 WO2014141620 A1 WO 2014141620A1 JP 2014001141 W JP2014001141 W JP 2014001141W WO 2014141620 A1 WO2014141620 A1 WO 2014141620A1
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Prior art keywords
acid
carbon atoms
electrolytic solution
solution according
electrolyte
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PCT/JP2014/001141
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English (en)
Japanese (ja)
Inventor
晋一 村田
清家　英雄
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三洋化成工業株式会社
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Application filed by 三洋化成工業株式会社 filed Critical 三洋化成工業株式会社
Priority to US14/774,697 priority Critical patent/US9793059B2/en
Priority to JP2015505264A priority patent/JP6371757B2/ja
Priority to CN201480011531.9A priority patent/CN105190809B/zh
Priority to EP14763901.7A priority patent/EP2975620B1/fr
Publication of WO2014141620A1 publication Critical patent/WO2014141620A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/08—Housing; Encapsulation
    • H01G9/10—Sealing, e.g. of lead-in wires
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/022—Electrolytes; Absorbents
    • H01G9/035—Liquid electrolytes, e.g. impregnating materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/145—Liquid electrolytic capacitors

Definitions

  • the present invention relates to an electrolytic solution for an aluminum electrolytic capacitor and an aluminum electrolytic capacitor using the same.
  • alkyl quaternary ammonium electrolytes were used.
  • the alkyl quaternary ammonium electrolyte has a problem in that liquid leakage occurs from a sealing portion deteriorated by alkali.
  • the amidine electrolyte solution disclosed in Patent Document 1 reacts with an alkali in which a compound having an alkyl-substituted amidine group is generated. Therefore, alkaline deterioration of the sealing body is suppressed, and the electrolytic solution does not leak from the sealing portion.
  • it since it has an effect which is not found in alkyl quaternary ammonium electrolytes, it is widely used as an electrolyte for aluminum electrolytic capacitors.
  • the subject of this invention is improving the reliability of an electrolytic capacitor so that electrolyte solution may not leak from a sealing part, even if the surrounding environment further heats up and a high humidity condition, maintaining high initial electrical conductivity.
  • the present invention comprises a solvent (A) and an electrolyte (D) represented by the following general formula (1), and includes a compound (E1) represented by the following general formula (2) and the following general formula (3).
  • R 1 to R 3 represent an alkyl group having 1 to 3 carbon atoms
  • R 4 to R 7 represent an alkyl group having 1 to 3 carbon atoms or a hydrogen atom
  • X ⁇ represents an anion of acid (C).
  • R 8 is an alkylene group having 1 to 3 carbon atoms
  • R 9 to R 12 are an alkyl group having 1 to 3 carbon atoms or a hydrogen atom.
  • R 11 and R 12 may be covalently bonded to form a ring.
  • R 13 is an alkylene group having 1 to 3 carbon atoms.
  • R 14 to R 17 are an alkyl group having 1 to 3 carbon atoms or a hydrogen atom.
  • R 16 and R 17 may be covalently bonded to form a ring.
  • R 18 is an alkylene group having 1 to 3 carbon atoms.
  • R 19 to R 22 are an alkyl group having 1 to 3 carbon atoms or a hydrogen atom.
  • R 20 and R 21 may be covalently bonded to form a ring.
  • the electrolytic capacitor using the electrolytic solution of the present invention is a highly reliable capacitor that does not leak the electrolytic solution from the sealed portion even at higher temperature and high humidity in the surrounding environment while maintaining high initial electrical conductivity. Can be.
  • the solvent (A) constituting the electrolytic solution of the present invention is preferably a polar solvent, more preferably a polar solvent (A1) having a relative dielectric constant of 5 to 150 at 25 ° C., and (A1 Among these, an aprotic solvent (A11) is more preferable.
  • Solvents (A) include (1) alcohol, (2) ether, (3) amide, (4) oxazolidinone, (5) lactone, (6) nitrile, (7) carbonate, (8) sulfone and (9) Other organic solvents are included.
  • Alcohol Monohydric alcohol methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol, diacetone alcohol, benzyl alcohol, amino alcohol, furfuryl alcohol, etc.
  • Dihydric alcohol ethylene glycol, propylene glycol, diethylene glycol, hexylene) Glycol, etc.
  • trihydric alcohol glycerin, etc.
  • tetravalent or higher alcohol hexitol, etc.
  • Ether monoether ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, tetrahydrofuran, 3-methyltetrahydrofuran, etc.
  • diether ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol
  • triether diethylene glycol dimethyl ether, diethylene glycol diethyl ether, etc.
  • Amide formamide N-methylformamide, N, N-dimethylformamide, N-ethylformamide, N, N-diethylformamide, etc.
  • acetamide N-methylacetamide, N, N-dimethylacetamide, N-ethylacetamide) N, N-diethylacetamide
  • propionamide N, N-dimethylpropionamide, etc.
  • pyrrolidone N-methylpyrrolidone, N-ethylpyrrolidone, etc.
  • hexamethylphosphorylamide etc.
  • Solvent (A) may be used alone or in combination of two or more. Of these, alcohol, ether, amide, lactone, nitrile, carbonate and sulfone are preferable, ⁇ -butyrolactone and sulfolane are more preferable, and ⁇ -butyrolactone is particularly preferable.
  • an aprotic solvent (A11) and a protic solvent (A2) such as ethylene glycol may be mixed.
  • the content of (A2) is 0 to 100% by weight (hereinafter sometimes referred to as wt%) based on the weight of (A11).
  • (A2) includes ethylene glycol, propylene glycol, diethylene glycol and the like.
  • the electrolyte (D) contained in the electrolytic solution of the present invention is a salt composed of an imidazolinium cation (D C ) and an anion (D A ) represented by the general formula (1).
  • R 1 to R 3 are alkyl groups having 1 to 3 carbon atoms
  • R 4 to R 7 are alkyl groups having 1 to 3 carbon atoms or a hydrogen atom. Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group.
  • imidazolinium cation examples include 1,2,3,4-tetramethylimidazolinium, 1,3,4-trimethyl-2-ethylimidazolinium, and 1,3-dimethyl-2.
  • 1,2,3,4-tetramethylimidazolinium and 1-ethyl-2,3-dimethylimidazolinium are preferable from the viewpoint of electrochemical stability.
  • Examples of the anion (D A ) include an anion of acid (C).
  • Examples of the acid (C) include various organic acids and / or inorganic acids that are usually used in an electrolytic solution.
  • Examples of the organic acid and inorganic acid include the following (1) to (6).
  • Carboxylic acids / C2-C15 divalent to tetravalent polycarboxylic acids aliphatic polycarboxylic acids [saturated polycarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, Speric acid, azelaic acid, sebacic acid, etc.), unsaturated polycarboxylic acids (maleic acid, fumaric acid, itaconic acid, etc.)], aromatic polycarboxylic acids [phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic Acid etc.], S-containing polycarboxylic acid [thiodibropionic acid etc.].
  • saturated polycarboxylic acids oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, Speric acid, azelaic acid, sebacic acid, etc.
  • Oxycarboxylic acid having 2 to 20 carbon atoms aliphatic oxycarboxylic acid [glycolic acid, lactic acid, tartaric acid, castor oil fatty acid, etc.], aromatic oxycarboxylic acid [salicylic acid, mandelic acid, etc.].
  • C1-C30 monocarboxylic acid aliphatic monocarboxylic acid [saturated monocarboxylic acid (formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, uraryl Acid, myristic acid, stearic acid, behenic acid, etc.), unsaturated monocarboxylic acids (acrylic acid, methacrylic acid, crotonic acid, oleic acid, etc.)], aromatic monocarboxylic acids [benzoic acid, cinnamic acid, naphthoic acid, etc. ].
  • saturated monocarboxylic acid (formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, uraryl Acid, myristic acid, ste
  • Phenols and monohydric phenols include phenols and naphthols: Phenol, alkyl (C1-15) phenols (cresol, xylenol, ethylphenol, n- or isopropylphenol, isododecylphenol, etc.) , Methoxyphenols (eugenol, guaiacol, etc.), ⁇ -naphthol, ⁇ -naphthol, cyclohexylphenol, etc.
  • Polyhydric phenol catechol, resorcin, pyrogallol, phloroglucin, bisphenol A, bisphenol F, bisphenol S, etc.
  • Mono- and dialkyl phosphate mono- and dimethyl phosphates having 1 to 15 carbon atoms in the alkyl group mono- and diethyl phosphate esters, mono- and diisopropyl phosphate esters, mono- and dibutyl phosphate esters, mono- and di-- (2-ethylhexyl) phosphate, mono- and diisodecyl phosphate, and the like.
  • a carboxylic acid (C11) having 1 to 15 carbon atoms (3) a monoalkyl phosphate ester having 1 to 15 carbon atoms, and a dialkyl phosphate ester having 2 to 30 carbon atoms and (5) Inorganic acids (C2) are preferred.
  • phthalic acid, maleic acid, mono and diethyl phosphate esters, mono and diisopropyl phosphate esters, mono and dibutyl phosphate esters, phosphoric acid, tetrafluoroboric acid, peroxy Chloric acid, hexafluorophosphoric acid, hexafluoroantimonic acid and hexafluoroarsenic acid are preferred.
  • phthalic acid and maleic acid are preferred.
  • Examples of the electrolyte (D) include the following. 1,2,3,4-tetramethylimidazolinium phthalate anion, 1-ethyl-2,3-dimethylimidazolinium phthalate anion, 1,2,3,4-tetramethylimidazolinium malein Acid anion, 1-ethyl-2,3-dimethylimidazolinium maleate anion, 1,2,3,4-tetramethylimidazolinium phosphate anion, 1-ethyl-2,3-dimethylimidazolinium Phosphate anion, 1,2,3,4-tetramethylimidazolinium diethylphosphate anion, 1-ethyl-2,3-dimethylimidazolinium diethylphosphate anion, 1,2,3 4-tetramethylimidazolinium diisopropyl phosphate anion, 1-ethyl-2,3-dimethylimidazolinium - diisopropyl phosphate ester anion, 1,2,3,
  • 1,2,3,4-tetramethylimidazolinium phthalate anion 1-ethyl-2,3-dimethylimidazolinium phthalate anion
  • 1,2,3,4-tetramethylimidazolinium malein Acid anion 1-ethyl-2,3-dimethylimidazolinium maleate anion.
  • the electrolytic solution for an aluminum electrolytic capacitor of the present invention contains an electrolyte (D) as a main electrolyte.
  • containing as the main electrolyte means that 50 wt% or more of the electrolyte contained in the electrolytic solution for electrolytic capacitors of the present invention is the electrolyte (D).
  • the electrolytic solution for an aluminum electrolytic capacitor of the present invention may contain an electrolyte (F) in addition to (D).
  • the content of (F) is less than 50 wt% of the electrolyte contained in the electrolytic solution for electrolytic capacitors of the present invention.
  • Examples of the electrolyte (F) include quaternary ammonium salts.
  • Specific examples include triethylamine / phthalate, ethyldimethylamine / phthalate, diethylmethylamine / phthalate, triethylamine / maleate, ethyldimethylamine / maleate, diethylmethylamine / maleate, etc. It is done.
  • the compound (E) constituting the electrolytic solution of the present invention is represented by the compound (E1) represented by the general formula (2), the compound (E2) represented by the general formula (3), and the general formula (4).
  • Specific examples of the compound (E3) include the following.
  • Compound (E) may be used alone or in combination of two or more.
  • 1,3,5-trimethyl-1,3-diazepan-4,7-dione, 1,4,6-trimethyl-1,4-diazepan-2,5-dione, 1,4,7 Trimethyl-1,4-diazepan-2,5-dione, 1,2,4-trimethyl-1,4-diazepan-5,7-dione are preferred.
  • the content of the compound (E) [the total content of the compounds (E1), (E2) and (E3)] is 3 wt% or less with respect to the total weight of the solvent (A) and the electrolyte (D). Furthermore, it is preferably 0.001 to 3 wt%, more preferably 0.005 to 2 wt%, still more preferably 0.01 to 1 wt%, and particularly preferably 0.01 to 0.5 wt%. is there. If it exceeds 3 wt%, the electrical conductivity of the electrolytic solution of the present invention will deteriorate.
  • the compound (E) is composed of the compound (E1), the compound (E2) and the compound (E3), and one or two or more of these may be used in combination.
  • the content of the compound (E) can be quantified by high performance liquid chromatography (HPLC).
  • HPLC measurement conditions are: column: packed with polymer-coated filler, mobile phase: phosphate buffer (pH 2-3), flow rate: 0.8 ml / min, detector: UV, temperature: 40 ° C. .
  • HPLC measurement conditions are: column: packed with polymer-coated filler, mobile phase: phosphate buffer (pH 2-3), flow rate: 0.8 ml / min, detector: UV, temperature: 40 ° C. .
  • What measured 100 times dilution of electrolyte solution with the mobile phase is made into the sample for a measurement.
  • water may be added to the electrolytic solution of the present invention.
  • the addition amount is 10 wt% or less based on the weight of the electrolytic solution from the viewpoint of heat resistance.
  • various additives usually used in the electrolyte can be added to the electrolyte of the present invention.
  • the additive include phosphoric acid derivatives (for example, phosphoric acid, phosphoric acid esters, etc.), boric acid derivatives (for example, boric acid, complex compounds of boric acid and polysaccharides [mannit, sorbit, etc.], boric acid and Complex compounds with polyhydric alcohols (ethylene glycol, glycerin, etc.), nitro compounds (eg, o-nitrobenzoic acid, p-nitrobenzoic acid, m-nitrobenzoic acid, o-nitrophenol, p-nitrophenol, etc.)
  • the amount added is 10 wt% or less based on the weight of the electrolyte from the viewpoint of the electrical conductivity of the electrolyte (D) and the solubility in the solvent (A).
  • an electrolytic solution for an aluminum electrolytic capacitor of the present invention a method of adding an electrolyte (D) to a solvent (A) and homogenizing by stirring, then adding a compound (E), stirring and mixing, etc. Is mentioned.
  • Phthalic acid (0.1 mol) is added to the methanol solution of 1-ethyl-2,3-dimethylimidazolinium methyl carbonate salt (0.1 mol) obtained above to give 1-ethyl-2,3-dimethylimidazole.
  • a methanol solution of linium phthalate anion was obtained.
  • the above solution was heated at a reduced pressure of 1.0 kPa or less at 50 ° C. until the distillation of methanol disappeared, the methanol was distilled off, the temperature was raised from 50 ° C.
  • 1-ethyl-2,3-dimethylimidazolinium phthalate anion was recrystallized using methanol and isopropanol to remove impurities (D-3) ⁇ 1-ethyl-2,3- Dimethylimidazolinium phthalate anion ⁇ was obtained.
  • 1,2,3,4-tetramethylimidazolinium diethylphosphate ester A monoanion was obtained.
  • the obtained 1,2,3,4-tetramethylimidazolinium diethylphosphate monoanion was recrystallized using methanol and isopropanol to remove impurities (D-4) ⁇ 1, 2, 3,4-tetramethylimidazolinium diethylphosphate monoanion ⁇ was obtained.
  • a methanol solution (74 wt%) of dimethyl carbonate (0.2 mol) and 5-methyl-1,3-diazepane-4,7-dione (0.1 mol) obtained above were mixed and stirred at 120 ° C. for 15 hours.
  • a methanol solution of 1,3,5-trimethyl-1,3-diazepan-4,7-dione was obtained.
  • 1,3,5-trimethyl-1,3-diazepane-4,7-dione (E1-1) was obtained by distilling off methanol at a reduced pressure of 1.0 kPa or less and 100 ° C.
  • Electrolytes (D-1) to (D-4) obtained in Production Examples 1 to 4 and compounds (E1-1), (E2-1), (E2-2) obtained in Production Examples 5 to 8 ), (E3-1), ⁇ -butyrolactone (manufactured by Mitsubishi Chemical) and sulfolane (manufactured by Sumitomo Seika) were mixed and dissolved in the blending amounts shown in Table 1, and Examples 1 to 36 and Comparative Examples 1 to 6
  • An electrolyte solution was prepared.
  • the content of the compound (E) is a measurement value measured under the following measurement conditions.
  • the content of the compound (E) is the content of (E) with respect to the total weight of the solvent (A) and the electrolyte (D).
  • a wound aluminum electrolytic capacitor (rated voltage: 6.3 V—capacitance: 220 ⁇ F, size: ⁇ 6.5 mm ⁇ L4.5 mm) was produced.
  • Peroxide-vulcanized butyl rubber was used as the sealing rubber.
  • the prepared aluminum electrolytic capacitor was applied with a rated voltage, and the state of the sealing body after 3000 hours was observed.
  • the conditions of temperature and relative humidity were as follows. Condition A; (temperature 105 ° C., relative humidity 85%), condition B; (temperature 130 ° C., relative humidity 85%), condition C; (temperature 140 ° C., relative humidity 85%)
  • the electrical conductivity of the electrolyte before the heat resistance test at 30 ° C. was measured using a conductivity meter CM-40S manufactured by TOA DK Corporation.
  • the electrolytic solution of the present invention does not leak from the sealed part even at higher temperatures in the surrounding environment or in humid conditions, and the electrical conductivity is excellent, so the reliability of the electrolytic capacitor Can be increased.
  • the electrolytic solution of the present invention is particularly useful for automotive applications in which the surrounding environment tends to be hot and humid.

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  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
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Abstract

La présente invention traite le problème d'augmenter la fiabilité d'un condensateur à électrolyte de telle manière qu'une conductivité électrique initiale élevée soit conservée sans fuite de la solution électrolytique même dans des conditions dans lesquelles la température augmente davantage, ou d'humidité significative dans l'environnement qui l'entoure. La présente invention porte sur une solution électrolytique destinée à être utilisée dans un condensateur électrolytique aluminium qui contient un solvant (A) et un électrolyte (D) indiquées par la formule générale (1), la teneur d'au moins un type de composé (E) sélectionné dans le groupe constitué par les composés (E1) à (E3) indiqués par les formules générales (2) à (4), respectivement, étant inférieure ou égale à 3 % en poids par rapport au poids total de ((A) et (D)). [Dans la formule, (R1) à (R3) sont des groupes alkyles ayant de 1 à 3 atomes de carbone, (R4) à (R7) sont des groupes alkyles ayant de 1 à 3 atomes de carbone ou sont des atomes d'hydrogène et X- est un anion (C) d'acide]. [Dans la formule, (R8) est un groupe alkyle ayant de 1 à 3 atomes de carbone. (R9) à (R12) sont des groupes alkyles ayant de 1 à 3 atomes de carbone ou sont des atomes d'hydrogène. De plus, (R11) et (R12) peuvent former une liaison covalente].
PCT/JP2014/001141 2013-03-12 2014-03-03 Solution électrolytique destinée à être utilisée dans un condensateur électrolytique aluminium et condensateur électrolytique aluminium qui utilise cette dernière WO2014141620A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US14/774,697 US9793059B2 (en) 2013-03-12 2014-03-03 Electrolytic solution for aluminum electrolytic capacitor and aluminum electrolytic capacitor using the same
JP2015505264A JP6371757B2 (ja) 2013-03-12 2014-03-03 アルミニウム電解コンデンサ用電解液、およびそれを用いたアルミニウム電解コンデンサ
CN201480011531.9A CN105190809B (zh) 2013-03-12 2014-03-03 铝电解电容器用电解液及使用其的铝电解电容器
EP14763901.7A EP2975620B1 (fr) 2013-03-12 2014-03-03 Solution électrolytique destinée à être utilisée dans un condensateur électrolytique aluminium et condensateur électrolytique aluminium qui utilise cette dernière

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JP2013-048598 2013-03-12
JP2013048598 2013-03-12

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US (1) US9793059B2 (fr)
EP (1) EP2975620B1 (fr)
JP (1) JP6371757B2 (fr)
CN (1) CN105190809B (fr)
TW (1) TWI598908B (fr)
WO (1) WO2014141620A1 (fr)

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JPH0449771B2 (fr) * 1984-12-21 1992-08-12 Nichikon Kk
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CN105190809A (zh) 2015-12-23
EP2975620B1 (fr) 2019-05-22
JP6371757B2 (ja) 2018-08-08
CN105190809B (zh) 2017-12-12
TWI598908B (zh) 2017-09-11
EP2975620A4 (fr) 2016-12-07
JPWO2014141620A1 (ja) 2017-02-16
US9793059B2 (en) 2017-10-17
EP2975620A1 (fr) 2016-01-20
US20160020036A1 (en) 2016-01-21

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